Olive Update: So much for being on a break

So much for being on a break, huh?

I can’t believe it has been more than a month since my last post on Christmas Eve. I apologize for that, but things have been 50 shades of busy and crazy. The Spring semester of college has started (only one more semester left after this), I’ve started looking for a job to get me through the Summer, my son and I are getting ready for baseball season, and things with Olive have been going very well.

I guess that’s what I should probably update you all on, since that’s pretty much the only reason you read this.

This update won’t be as much of a date night play-by-play as the others, but more of a encapsulated overview. And I’ll try to make it short and sweet since a lot has happened since my last post.

Olive and I met literally on New Year’s Day, after more than a month of emailing and talking. The Holidays really got in the way of us finding time to meet. My Match subscription ended at the end of December, and as I stated previously, I was done dating for a while and was going to take a break.

Maybe I should have quit and given up sooner, because once I did, Olive entered the picture and totally blew me away. She had to in order for me to forego my Holiday Hiatus.

She’s a sweet, blonde, country girl with a rock-hard body because she is crazy into fitness and works out every day. She may look small but she’s all muscle which makes her surprisingly heavier than you’d expect. She has a son about the same age as my little guy, and they get along famously. Yes, at this point, we’ve met each others’ kids and they’ve met each other.

Things started off real slow and easy, due in part to scheduling issues, but once we started seeing each other, it became more and more regular and with greater frequency. At this point, she’s over every Wednesday when her son is spending time with his father, and pretty much all weekend whether she has her son or not.

Things were going so well with her, I was more cautious trying not to mess things up. It took several visits together before we actually kissed and then much longer before we actually slept together. Then again, my schedule with my son probably played a big part in that because I don’t have a lot of free nights with him around and we’re not having “adult sleepovers” with him in the house.

For the first time since starting this dating journey, I’m actually willing to call someone my girlfriend and start to make plans for things more than just a week or two out. Like my son is very excited to go to her parent’s farm where all of her horses are, which we are putting on hold until the weather gets better. Freezing temps and snow don’t make horseback riding very enjoyable. We’ve also signed up for some running road races together. So, that’s a good sign she’s willing to do that and I’m not freaking out about it.

And yes, we have plans for next weekend, but NOT on Valentine’s Day – per se. We might be together, but not making any plans or going out. Go figure, the one holiday I was most trying to avoid with a new girlfriend, and here I am, caught in the trap.

This weekend I’ll post the update about the conversation with my ex-wife when I told her about Olive. Just reinforces why I’m glad I’m not with her anymore.

I hope you’re all staying warm and not buried in too much snow.

Til later!

Christmas Eve ramblings and updates

Merry Christmas and Happy Holidays to everyone!

Since I’m sitting at my parent’s house (totally bored) alone with my sons are with their mothers this year, I figured I’d catch you all up on how things are going.

I told you I pretty much put dating on hold over the Holidays, so … of course, what happens? Yep, multiple interests come seeking me out. Never fails.

I seriously contemplate just forgetting about actively dating because when I ignore the “dating game” prospects just come to me (somehow).

I’ve had two serious prospects over the last week or so. Both contacted me on Match and I’ve been talking with both since. Naomi, is a petite, 40-something CPA, mother of 3; and Olive is my age, a classic country girl with a son about the same age as my youngest son.

Things with Naomi were a little too aggressive and moved a bit too fast. We’d been taking for about a week when I took my son to his mom’s. She was very aggressive in saying how much she was thinking about me and talking about plans and stuff already. This is all before we’ve even met yet. So on my way back from dropping my son off, she called and we talked almost the entire 4-hour trip back. Then she basically invited herself over to meet me at my house when I got home (about 1 a.m.).

We both had to work the next day, but I figured “what the hell, why not?” She met me near my house and followed me home. Honestly, once we got to my place, I figured we’d chat for a while and she’d go home. I was wrong. I grabbed us both some water in the kitchen when she came in and grabbed me and started making out with me. She dragged me to the couch for some more making out, then suggested we go upstairs to the bedroom.

Ok. This was moving a bot way too fast for something that would have any chance of being a serious relationship. But I’m a guy, it’s not like I’m gonna really say NO and stop things. My chances at this are too far and few between.

After a vigorous round of bedroom aerobics, she stayed and cuddled til we both fell asleep. She stayed until about 5 a.m., when she got up to leave and get ready for work. All the next day she texted and called repeatedly. Over the next few days, the conversations trailed because she was becoming too clingy and we hadn’t even really gone a date yet. I was getting highly annoyed, and just couldn’t take it much more. So I told her I wasn’t sure things were working out, maybe we should slow it down a bit and see what happens. It’s been a few days and I haven’t heard from her since.

I haven’t met Olive yet, in person, but we talk every day. She’s very sweet and we have so much in common and our little boys seem almost identical. So far, if there’s a problem of any kind, it’s that our schedules have been seriously conflicting so we haven’t been able it meet yet. It’s not a serious issue since we’ve only been trying for about a week to find a time. But she had her son when I was free and now that he’s visiting his father’s, I’m visiting my family out of town.

But as I’ve been writing this, Olive has been texting me the whole time because she’s bored bad wants me to keep her company.

I am a little paranoid about dragging this out about another week or so, because the last time this happened, coincidentally over the Christmas break, the girl I was into moved on (back to her ex-husband) before I really even had a chance.

But I guess, as they say, “things happen for a reason.” Maybe this one will work out better than that one.

I’m going to sign off for now. “It’s A Wonderful Life” and a 24 hours of “A Christmas Story” are on.

Merry Christmas and Happy Holidays to you all, and thanks again for reading.